1,1'-Carbonyldiimidazole → N-[1-[4'-(3-Methyl-4-phenethylsulfanylmethyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarbonyl]-methanesulfonamide

HRID 1512688Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1512688
[CH3:1][C:2]1[C:6]([CH2:7][S:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:5]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4([C:32]([OH:34])=O)[CH2:31][CH2:30]4)=[CH:25][CH:24]=3)=[CH:19][CH:18]=2)[O:4][N:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:47][S:48]([NH2:51])(=[O:50])=[O:49].CCN(C(C)C)C(C)C>O1CCOCC1>[CH3:1][C:2]1[C:6]([CH2:7][S:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:5]([C:17]2[CH:18]=[CH:19][C:20]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4([C:32]([NH:51][S:48]([CH3:47])(=[O:50])=[O:49])=[O:34])[CH2:30][CH2:31]4)=[CH:25][CH:24]=3)=[CH:21][CH:22]=2)[O:4][N:3]=1

Komponenten

6

Edukt 4

HCID 682631,1'-CarbonyldiimidazoleHCID 72879MethanesulfonamideHCID 81531DiisopropylethylamineHCID 513523511-[4'-(3-Methyl-4-phenethylsulfanylmethyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid

Produkt 1

HCID 51352174N-[1-[4'-(3-Methyl-4-phenethylsulfanylmethyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarbonyl]-methanesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

1-[4′-(3-Methyl-4-phenethylsulfanylmethyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid (0.2 g, 0.43 mmol) was dissolved in dioxane along with carbonyldiimidazole (0.2 g, 1.23 mmol), methanesulfonamide (0.14 g, 1.47 mmol) and Hünig's base. The reaction was heated to reflux overnight then cooled and submitted to standard aqueous workup. The residue was purified via silica gel chromatography (0-60% EtOAc in hexanes) to give the title compound.

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. temperaturethen cooled
  4. customThe residue was purified via silica gel chromatography (0-60% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-cf7bd963b58344f7b4a154cd5e3d0d57
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08217066B2

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